Upgrading Questions

I know that some time in the future I'm going to upgrade both my machine and the grinder, whether separately or at the same time (i.e. I've seen deals on the Rancilio syliva/rocky combo with base). I don't know what I want but was hoping that there is a guide out there to help one sort this out???

I have an inexpensive Breville espresso machine and Krups grinder. With fresh roasted coffee and improvements to my dosing/tamping skills, I'm getting all I can out of these machines.

My current use is a double espresso or macchiato each week night, and 2 to 3 drinks each day on the weekend. I'm usually only making drinks for myself, but once a month we'll have someone over who would like a cappuccino or espresso (up to 3 people including me at the most). I don't really have time to clean the machine after each use, but I do and at the same time piss off my wife. I would have a drink in the morning if it didn't take much time (prep/brew/clean is too much for the morning for me).

I don't have a budget per say, but my current set-up cost $250 Canadian, so I don't think I'll increase my budget 10X over, but maybe to around $1,000 (either spaced out with 2 separate purchases or one leap).

I'm not an espresso expert, meaning I don't need the best shot in the world every time...heck I'm fairly happy with my current shots.

Anyway, I know it's a long post but I would appreciate any links/tips.

Well, from all your info I'd tell you to get an automatic. You can find decent machines that do pretty much everything for you for the money you want to spend. You won't have to do much cleaning and you can get decent shots from them. Some are programmable and will come on when you want them to. More expensive units will steam/froth milk for you as well as alot of other tasks. They can be handy if you don't really care for the hands on experience that other machines require.

I like to control all things espresso related and don't mind the cleanup. I have a KitchenAid Pro Line espresso machine and grinder and get outstanding results and because of the deals I found on them I only have about $600 (US) invested for everything (machine, grinder, tamper, cups, etc.).

Later!

I'm a legend among my own kind... you my friend are just a legend in your own mind. Later!

The coffeegeek website has LOTS of reviews and information regarding consumer grade espresso brewers and grinders.
I like the doserless espresso grinders for infrequent use, and some of the commercial grade models are in your price range.